Mille Miglia Race

Searing hot brakes, maxed-out rpm, super-hot babes. European automobile manufacturers have spent a century creating phenomenal cars built specifically for the purpose of hitting the road without concern for speed limits. Car-lover or not, there’s something undeniably sexy about this culture. Racing is the ultimate gentleman’s sport – a very literal translation of speed-dating. So we felt it was time to explore Mille Miglia, a 1,000-mile open-road endurance race from northern Italy to Rome and back. We asked Roger, our token world-traveling, model-dating, up-for-anything writer, if he’d be game to driving the route – in a Ferrari. It didn’t take much convincing.

The Background

The Mille Miglia has a long-standing reputation as the most glorious of Europe’s great car races, with beauties like Alfa Romeo Spiders and Ferrari Berlinettas gracing the winners' podium. It was established as a way to put Brescia, the birthplace of Italian motor sport, back on the map after the Italian Grand Prix moved to Monza in 1922.

Dubbed by Enzo Ferrari as "the world's greatest road race,” the Mille Miglia was first raced in 1927, with 51 out of 77 sports cars crossing the finish line. The race quickly became known as one of the most dangerous of European rallies, thriving for several decades until the Italian government declared an end to motor racing on public roads in 1957, when one of the cars spun out, killing a dozen people.

In 1927, the entry fee was one lira – a real steal. Today it costs upwards of $10,000 per car. And rightfully so. There’s a whole lot to love about driving across Italy’s breathtaking landscapes in a vintage car, especially one manufactured between 1927 and 1957 that took part in the original race. The 1,000-mile rally runs from Brescia to Rome, through Modena, Florence, Siena, and Pienza, past the vineyards of Chianti and Montepulciano, and through quaint Tuscan settlements like Poggibonsi, Buonconvento, and Radicofani.

Here’s the thing: These days, it’s a little more “celebrity-and-old-guy car show” than “grueling competition.” And while that’s charming in its own right, if I’m going to drive through Italy in a sweet ride, I don’t want to forgo, say, food, wine, and culture. So I decided to spend a week following the Mille Miglia route, navigating my way through the windy roads of central Italy, on my own terms and at my own pace. (Read: fast.)

The Car

“La Ferrari si guida come se fosse una cosa viva,” Simonetta Troisi cautions me as I lower myself into the leather cockpit of her fire-engine-red 308 GTS. With that, I embrace my new motoring mantra: Ferraris should be driven as though they’re alive. “And don’t drive at 50 in fourth gear,” she adds, as I ease the car out of its holding pen and onto a winding country road. A woman who lends you her vintage sports car and implores you to gun it clearly knows the way to a man’s heart. I was empowered. I may not be able to grow Tom Selleck’s chest hair, but I’d be damned if I wasn’t going to helm Magnum, P.I.’s thundering GTS.

And here’s another thing: A Ferrari is a little like Sophia Loren. It’s insanely sexy, but it requires real finesse to handle. Cars like this were built at a time when a luxury automobile meant real metal and craftwork. This car was designed to be muscled around the sharp corners of Tuscan hills, the driver gripping the burled-walnut steering wheel as tightly as the tires grip the road. Which is awesome. But it also means that this car is heavy. Like really heavy. Due to the rutted state of the country roads, I only feel comfortable flooring it once I make it onto the freeway, which is slightly defeating. But perched in that tan bucket seat, I regain my confidence. I play with the three-liter mid-engine V8, its thunder resonating in the cockpit. When I finally open up the throttle, I’m off, flying past stone villas, olive groves, and umber fields. And this is just practice.

The Route

I start where the Mille Miglia begins, in Brescia, a cosmopolitan city of Roman ruins and Renaissance squares where the Alpine meets the Mediterranean. I speed south to Ferrari’s hometown of Modena, where a museum dedicated to the life of Enzo Ferrari has recently opened. The bright-yellow structure holds scores of classic cars, racing memorabilia, historical documents, and evocative black-and-white video footage of fast cars in action. I pay my respects.

Further south in Florence, I drop my bags at the Savoy and head out to gorge on local pici, a chewy Siennese hand-rolled pasta, and discover that it provides a solid foundation for another preferred sport: designated drinking. Good thing that in addition to truffles, wild boar, and romantic villas, Tuscany is also known for its Brunellos and Chiantis.

I continue south, overnighting in Tuscany’s rural guesthouses. Follonico B&B’s half-dozen suites have small pebbled porches and superior views out to the surrounding valley. Siena House, a crackerjack four-room farmhouse, has original stone floors, large shuttered windows, abstract art, and a saltwater infinity pool. Before looping back towards Brescia, I stop at the medieval frescos of the clifftop Monte Oliveto Maggiore Abbey, ducking into the monks’ cafe for an herbal liqueur tasting. (And yes, even the celibate monks ogle my car. It has that kind of power.)

The Finish Line

Outside of Tuscany, the 255hp GTS really hits its groove – especially once I discover I’m late for my flight. When you have a plane to catch, there’s no other car you want to be driving. With the sun setting behind me, I check the rearview mirror, depress the counterweighted pedal to the floor, and let the car transport me, warp speed, towards the runway.

Emerald expressway. Violet sunset. Black Persols. Red Ferrari. If there is a single better way to travel, I have yet to find it.